Transcript Are You Getting It??
BIOCHEMISTRY REVIEW Overview of Biomolecules Chapter 7 Carbohydrates
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MONOSACCHARIDE PROPERTIES
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WHITE SOLIDS POLAR- SOLUBLE IN WATER FORMULA = (CH
2
O)
n
where n = 3-7 UNBRANCHED CARBON SKELETON ONE CARBONYL GROUP ALL OTHER CARBONS HAVE HYDROXYL CLASSIFIED AS ALDOSE OR KETOSE CLASSIFIED BY NUMBER OF CARBONS
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____________________________________________________ ____________________________________________________ Which of the following structures are monosaccharides?
(multiple answers)
a) CHO b) CHO c) CH 2 OH d) CHO | | | | CHOH CHOH C = O CH 2 | | | | CHOH CHOH CHOH CHOH | | | | CH 2 OH COOH CH 2 OH CH 2 OH
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____________________________________________________
______________________Answer________________________
Which of the following structures are monosaccharides?
a) CHO | CHOH | CHOH | CH 2 OH b) CHO c) CH 2 OH | | CHOH C = O | | CHOH CHOH | | COOH CH 2 OH d) CHO | CH 2 | CHOH | CH 2 OH
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D-erythrose D-threose L-threose L-erythrose CHO CHO CHO CHO | | | | H – C – OH HO – C – H H – C – OH HO – C – H | | | | H – C – OH H – C – OH HO – C – H HO – C – H | | | | CH 2 OH CH 2 OH CH 2 OH CH 2 OH
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____________________________________________________ ____________________________________________________ Consider an aldopentose: HOH 2 C - (CHOH) 3 - CHO a) How many carbonyl groups does it contain?
b) How many primary alcohols does it contain?
c) How many stereogenic centers does it contain?
d) How many aldopentoses exist?
e) How many D-aldopentoses exist?
f) How many L-aldopentoses exist?
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____________________________________________________
_____________________Answer________________________
Consider an aldopentose: HOH 2 C - (CHOH) 3 - CHO a) How many carbonyl groups does it contain?
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b) How many primary alcohols does it contain?
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c) How many stereogenic centers does it contain?
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d) How many aldopentoses exist?
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e) How many D-aldopentoses exist?
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f) How many L-aldopentoses exist?
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____________________________________________________ ____________________________________________________ D-ribose is an aldopentose. CHO The C-3 epimer of D-ribose is |
(multiple answers)
H – C – OH a) another aldopentose | b) a ketopentose H – C – OH c) an enantiomer of D-ribose | d) a diastereomer of D-ribose H – C – OH e) an L-pentose | f) a D-hexose CH 2 OH
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____________________________________________________
______________________Answer________________________
D-ribose is an aldopentose. CHO The C-3 epimer of D-ribose is | H – C – OH
a) another aldopentose
| b) a ketopentose H – C – OH c) an enantiomer of D-ribose |
d) a diastereomer of D-ribose
H – C – OH e) an L-pentose | f) a D-hexose CH 2 OH
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D-erythrulose L-erythrulose
CH 2 OH CH 2 OH | | C = O C = O | | H – C –
OH HO
– C – H | | CH 2 OH CH 2 OH
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____________________________________________________ ____________________________________________________ Consider a ketohexose: HOH 2 C - (CHOH) 3 - C - CH 2 OH ║ O a) How many carbonyl groups does it contain?
b) How many primary alcohols does it contain?
c) How many stereogenic centers does it contain?
d) How many ketohexoses exist?
e) How many D-ketohexoses exist?
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____________________________________________________
_____________________Answer_________________________
Consider a ketohexose: HOH 2 C - (CHOH) 3 - C - CH 2 OH ║ O a) How many carbonyl groups does it contain?
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b) How many primary alcohols does it contain?
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c) How many stereogenic centers does it contain?
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d) How many ketohexoses exist?
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e) How many D-ketohexoses exist?
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OXIDIZING AGENTS
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Benedict’s Reagent- alkaline Cu
2+
+ citrate
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Fehling’s Reagent- alkaline Cu
2+
+ tartrate
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Tollen’s Reagent- alkaline Ag
+
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OXIDATION BY BROMINE WATER CHO COOH | | (CHOH)
n Br 2 + H 2 O
|
(CHOH)
n
| CH
2
OH CH
2
OH
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PERIODATE OXIDATION GROUPS MONOSACCHARIDES OH
C=O
C=O
ONE HIO 4 PER C-C BOND
COOH
ONE HCHO PER 1 O OH
COOH
CO
2 ONE HCOOH PER 2 O OH ONE HCOOH PER ALDEHYDE ONE CO 2 PER KETONE
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PERIODATE OXIDATION OF GLUCOSE CHO HCOOH | H – C – OH HCOOH | HO – C –H HCOOH | 5 IO 4 – 5 IO 3 – H – C – OH
HCOOH | H – C – OH HCOOH | CH 2 OH HCHO
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____________________________________________________ ____________________________________________________ Which oxidations and reductions can occur with monosaccharides?
(multiple answers)
a) Primary alcohols can be oxidized into aldehydes.
b) Aldehydes can be reduced into acids.
c) Secondary alcohols can be oxidized into acids.
d) Ketones can be oxidized into alcohols.
e) Aldehydes can be reduced into alcohols.
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____________________________________________________
______________________Answer________________________
Which oxidations and reductions can occur with monosaccharides?
a) Primary alcohols can be oxidized into aldehydes.
b) Aldehydes can be reduced into acids.
c) Secondary alcohols can be oxidized into acids.
d) Ketones can be oxidized into alcohols.
e) Aldehydes can be reduced into alcohols.
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HAWORTH STRUCTURES
CHO CHO HO – C – H OH OH OH HO HO HO OH OH OH OH HOH 2 C HOH 2 C CH 2 OH OH O H –C- OH CH 2 OH CH 2 OH OH O O OH HO OH OH OH HOH 2 C HO OH HO O OH OH α β
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____________________________________________________ ____________________________________________________ When an aldohexose forms a ring structure,
(multiple answers)
a) the ring contains 5 carbons and 1 oxygen.
b) the hemiacetal bond is stable.
c) the ring is planar.
d) C-1 becomes chiral.
e) the reaction is between two alcohols.
f) the two anomeric forms are mirror images.
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____________________________________________________
______________________Answer________________________
When an aldohexose forms a ring structure,
a) the ring contains 5 carbons and 1 oxygen.
b) the hemiacetal bond is stable.
c) the ring is planar.
d) C-1 becomes chiral.
e) the reaction is between two alcohols.
f) the two anomeric forms are mirror images.
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____________________________________________________ ____________________________________________________ When a ketohexose forms a ring structure,
(multiple answers)
a) the ring is a furanose.
b) the bond formed is a hemiketal.
c) the reaction involves the ketone group.
d) the orientation of all the OH groups changes.
e) a new stereogenic center is created.
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____________________________________________________
______________________Answer________________________
When a ketohexose forms a ring structure,
a) the ring is a furanose.
b) the bond formed is a hemiketal.
c) the reaction involves the ketone group.
d) the orientation of all the OH groups changes.
e) a new stereogenic center is created.
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____________________________________________________ ____________________________________________________ Which are properties of an acetal/ketal bond?
(multiple answers)
a) The bond is stable at neutral pH.
b) The bond is stable at acidic pH.
c) The bond forms when an alcohol reacts with a hemiacetal/hemiketal.
d) The bond can mutarotate.
e) The bond can be part of a monosaccharide.
f) The bond can be part of an oligosaccharide.
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____________________________________________________
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Which are properties of an acetal/ketal bond?
a) The bond is stable at neutral pH.
b) The bond is stable at acidic pH.
c) The bond forms when an alcohol reacts with a hemiacetal/hemiketal.
d) The bond can mutarotate.
e) The bond can be part of a monosaccharide.
f) The bond can be part of an oligosaccharide.
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N-GLYCOSIDE
CH 2 OH O OH HO NHCH 3 OH
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O-ACYL DERIVATIVE
CH 2 OCH 3 O OCH 3 H 3 CO OCH 3 OCH 3
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____________________________________________________ ____________________________________________________ Which characteristics are found in monosaccharide derivatives?
(multiple answers)
a) They can contain nitrogen.
b) They have the formula (CH 2 O) n .
c) They can be negatively charged.
d) They always are ring structures.
e) They can be formed by oxidizing or reducing monosaccharides.
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____________________________________________________
_______________________Answer_______________________
Which characteristics are found in monosaccharide derivatives?
a) They can contain nitrogen.
b) They have the formula (CH 2 O) n .
c) They can be negatively charged.
d) They always are ring structures.
e) They can be formed by oxidizing or reducing monosaccharides.
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STRUCTURAL DETERMINATION OF MALTOSE BROMINE WATER / DIMETHYL SULFATE / ACID CH 2 OCH 3 COOH O (OH) OCH 3 OCH 3 H 3 CO H 3 CO OH OH OCH 3 OCH 3 CH 2 OCH 3
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____________________________________________________ ____________________________________________________ Which are properties of maltose?
(multiple answers)
a) It is composed of two aldohexoses.
b) It is a non-reducing sugar.
c) It can mutarotate.
d) It can exist as α-maltose or β-maltose.
e) It can have an α-glycosidic bond or a β-glycosidic bond.
f) It contains a hemiacetal bond.
g) It contains an acetal bond.
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____________________________________________________
______________________Answer________________________
Which are properties of maltose?
a) It is composed of two aldohexoses.
b) It is a non-reducing sugar.
c) It can mutarotate.
d) It can exist as α-maltose or β-maltose.
e) It can have an α-glycosidic bond or a β-glycosidic bond.
f) It contains a hemiacetal bond.
g) It contains an acetal bond.
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____________________________________________________ ____________________________________________________ Which are properties of disaccharides?
(multiple answers)
a) They are all reducing sugars.
b) They are all composed of aldoses.
c) They all contain a glycosidic bond.
d) They all have anomeric forms. e) They all have 1,4 bonds.
f) The two monosaccharide components can be the same or different.
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____________________________________________________
______________________Answer________________________
Which are properties of disaccharides?
a) They are all reducing sugars.
b) They are all composed of aldoses.
c) They all contain a glycosidic bond.
d) They all have anomeric forms. e) They all have 1,4 bonds.
f) The two monosaccharide components can be the same or different.
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____________________________________________________ ____________________________________________________ Which can be a characteristic of a polysaccharide?
(multiple answers)
a) It can contain one type of monosaccharide component.
b) It can contain different types of glycosidic bonds.
c) It can contain monosaccharide derivatives.
d) It can have an unbranched structure.
e) It can function in energy storage.
f) It will have a precise molecular weight.
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____________________________________________________
______________________Answer________________________
Which can be a characteristic of a polysaccharide?
a) It can contain one type of monosaccharide component.
b) It can contain different types of glycosidic bonds.
c) It can contain monosaccharide derivatives.
d) It can have an unbranched structure.
e) It can function in energy storage.
f) It will have a precise molecular weight.
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_________________________________________________________ _________________________________________________________ Which characteristics are found in glycogen , cellulose , or both?
a) It contains α-glycosidic bonds.
b) It contains β-glycosidic bonds.
c) It contains 1,4-glycosidic bonds.
d) It contains hydrogen bonds.
e) It has a fibrous structure.
f) It has a branched structure.
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_________________________________________________________
_________________________ Answer _________________________
Which characteristics are found in glycogen , cellulose , or both?
a) It contains α-glycosidic bonds.
glycogen
b) It contains β-glycosidic bonds.
cellulose
c) It contains 1,4-glycosidic bonds.
both
d) It contains hydrogen bonds.
both
e) It has a fibrous structure.
cellulose
f) It has a branched structure.
glycogen
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